Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds.
An efficient and original stereocontrolled transannular rearrangement starting from activated 2,5-diketopiperazines has been developed, an opportunity for the medicinal chemistry field, which requests access to novel biological scaffolds. This powerful ring contraction, which can be related to a stereoselective aza-version of the Chan rearrangement, allows for example the one-step synthesis of various tetramic acids, access to 2-disubstituted statins, or the synthesis of relevant lactam-constrained dipeptide mimetics using a TRAL-RCM sequence.
Farran
Daniel
D
Institut des Biomolécules Max Mousseron, UMR CNRS 5247, Université Montpellier 1, Université Montpellier 2, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France.
Parrot
Isabelle
I
Toupet
Loïc
L
Martinez
Jean
J
Dewynter
Georges
G
D000478:Alkylation; D040761:Biomimetic Materials / Q000138:chemical synthesis; D004151:Dipeptides / Q000138:chemical synthesis; D007769:Lactams / Q000737:chemistry; D010879:Piperazines / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D004151:Dipeptides; D007769:Lactams; D010879:Piperazines